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Author's Note: This story will be my submission into Kasarberang's non-con contest! I strongly encourage you to go to his original post to see the rules and get a better summary of the expected content of this story. This is just the start of this story, but I hope to have it finished by the deadline for the contest, if not that, then the majority will be written in accordance with the guidelines. This chapter will only have hints of what is to come, but it is very sexually graphic. Please take this as a warning to those who do not like that kind of thing. It will get worse. Heed all my tags as I will be tagging all the relevant things for this story all at once rather than as the story progresses. Please enjoy! Boss Baby or Boss' Baby? : Chapter 1 “Here you go, Baby,” Miss Tammy said sweetly. Jesse blinked as his focus on his computer was broken and turned to Miss Tammy to see her holding a small plate with two donuts stacked on top. The workday had just started and he’d been sending out a few follow-up emails from the previous day when Miss Tammy approached. Seeing that she had his attention, she continued speaking. “I bought donuts for the office but I wanted to make sure you had some while they were still warm,” She smiled and set the plate down on the edge of his desk. “I also grabbed some milk for you.” She put the small bottle of milk right beside the plate. “Eat up!” Jesse’s eyes lit up. He didn’t often have breakfast in the morning, but he’d devour anything given to him by Miss Tammy. Miss Tammy was the supervisor over the whole department. A woman of 35 (her birthday had just passed– They sang to her with cupcakes in the breakroom.) with a strict standard but soft heart. She could easily portray the tough boss aura, but that disappeared as soon as she slipped on her trademark black cardigan and red reading glasses. Said glasses were perched on top of her head, the stems hooked into locks of blonde hair tied in a bun so that they didn’t fall. She must have left her cardigan in her office, Jesse noted as he stood up to hug her in thanks. He was shorter than her on a good day, but now, with her wearing her standard black heels, she was tall enough to tuck his head under her chin and nearly inappropriately close to her bust. “Thank you, Miss Tammy!” Jesse smiled. “That was really sweet of you!” “Oh hush,” She giggled, squeezing Jesse firmly before letting him go. “You know you’re my favorite.” The wink she followed the statement with had him returning the laugh. It was a running joke in the office that Jesse was her favorite employee because of the way she constantly doted on him. Jesse summed it up to being the youngest worker on the floor at just 21 years old. The next person older was Samantha at 25. It didn’t hurt that he leaned into the presumed special treatment by calling her ‘Miss Tammy’. The name was a bastardization of ‘Tammy’ the nickname the other supervisors called her, and ‘Miss Tamera’ the respectful title used by the rest of the floor. The first time he’d used it was an accident, but the resulting coo and sincere hug encouraged him to keep it up. “Oh! Before I forget,” She snapped, suddenly reminding herself of something. Jesse had since sat down at his desk and paused with half a bite of sugary glazed donut stuck in his mouth. “We are doing drug tests later on today starting after lunch.” The words made Jesse’s stomach drop. “W-What?” He stuttered. Miss Tammy carried on as if she didn’t notice his hesitance. “You know how the janitors found weed stashed in the cleaning supplies closet?” She waited for his nod before speaking, leaning against the wall of his cubicle. “Well, I told John,” John Scott, who was her boss. “That none of my employees would ever bring something like that into the building. I even told him that it was probably one of the new janitors!” That led her to a laugh, head tossed back enough that she had to catch her red reading glasses before they fell from her head. “But he was insistent that everyone on the floor get drug tested. Even IT down the hall is getting it done,” She sighed. “Uh,” He wiped the crumbs from his lip, not feeling so hungry any longer. “What happens if someone…fails?” Miss Tammy’s face took on a sad look. “John says they’re getting fired, but if anyone on the floor tests positive, I’ll make my case for them. I love my team so far, I’d hate to see anyone go.” “Yeah,” Jesse cleared his throat after his voice cracked, taking a sip of milk to rinse his mouth. “That would be bad…” “Mhm,” Miss Tammy spared a distant look at him before coming back to her usual chipper self. “But keep that between us, okay, baby?” The pet name a joke just as his own for her. “It’s supposed to be a surprise.” “I will,” He assured, turning back to his computer. He nearly felt a bead of sweat drip down his forehead. “Thanks again for the donuts…” It’ll be the last donuts he ever receives from her, he’s sure. It wasn’t that he was a smoker. He wasn’t! It was just…a stupid party. That weekend was his brother Travis’ birthday and they’d all taken a camping trip to celebrate. It was a great time with swimming at the lake, roasting marshmallows, and grilling hot dogs that Jesse…well. The blunts were passed around before he could even register it. One ended up in his hand…Travis said he didn’t have to, of course, but the cajoling of his (older than Jesse) friends pressured him into taking a drag. The smoke was awful! Jesse was wheezing and almost felt like he would throw up, much to the amusement of the crowd. When the next blunt came around, he told himself he’d pass it down. But Amber, the friend of Travis’ girlfriend, grabbed him by the chin and shotgunned the smoke in the pantomime of a kiss into his mouth. The hoots and hollers of the crowd spurred him on passed the lesser coughs that came from the lungful. The rest of the night was spent in the company of family and friends alike. And each puff after was like riding a bike. It was the first time Jesse had ever been high…and it was the best weekend of his life so far. But now… He’d be fired! Dread settled so deep in his stomach that he couldn’t work on anything as the office slowly filled with people. Two hours passed, only one more til lunch and then his fate would be sealed. Jesse’s hands were clammy with sweat. Should he just leave? Pretend he was sick and go? That would only delay the inevitable. And Miss Tammy would know he was lying! She’d seen him just this morning. No…He had to tell her before it was too late. Honesty was the key. He wasn’t the one who left the weed in the closet, of course. She would know that! She’d believe his story and she already said she was willing to plead his case to John. Newly emboldened, Jesse shot out of his chair and nearly tripped over his wastebasket on his way to Miss Tammy’s office. He felt the sweat on his face cooling at his quick movements and didn’t even stop to think about what his coworkers would think. A few quick knocks on the cracked door and he barely waited for the “Come in!” before slipping inside and shutting the door behind him. Miss Tammy sat at her desk, glasses perched low on her nose, and her eyes widened when she saw him. “Jesse? Are you alright?” She asked with full concern and turned her full attention to him. “Sit! You look like you’re going to be sick.” Jesse took the seat in front of her desk with slumped shoulders. “Miss Tammy I screwed up,” He said weakly. Tears rushed to his eyes as the events caught up with him. “Baby,” She said softly, her bracelet scratching lightly against the wooden desk as she leaned against it. “Talk to me, what has you all ruffled? Whatever it is, I’m sure it’s okay.” “It’s not!” Jesse gasped. “I’m gonna fail the drug test.” At the admission, he slumped forward with his elbows on his knees and sobbed. “I smoked this weekend. I’m going to fail! I’m so sorry!” “Woah,” She kept her calm tone, the sound of her chair rolling back cut through the air. “Take a breath, baby.” Her advice came soft as she walked around the desk. Jesse could see her bare feet where she’d taken off her heels in the privacy of her office. From the vantage point, he could also see a plastic wastebasket being positioned in front of him. If he finished those donuts, he most definitely would have been using it. A gentle hand rested between his shoulder blades and rubbed in circles soothingly. “Breath for me.” The breaths came shaky, but they helped slow the tears dribbling from his eyes and making dark spots on her grey carpet. Fuck, he was a mess. “I’m sorry,” He whispered again. “Don’t worry, baby,” She said immediately. “I don’t want to get fired!” He looked up finally, casting his blurry vision onto her face, mere inches away from his from where she leaned over. “I- I don’t smoke- It was just one time!” “I know,” She nodded. “I know you don’t smoke. You said it was a party. These things happen-” “I’m so sorry-” “I’m not angry with you,” She said for the first time in a firm tone, her brows furrowed and lips pursed. “I’m not, baby. I’m just worried you’ve worked yourself into this state.” Jesse’s lip quivered again and he watched her reach over her desk for a tissue. His hand reached up to receive it but was ignored in favor of her dabbing at his wet cheeks. His vision cleared up and to avoid meeting her analytic eyes, he stared ahead, only to flinch as he was rewarded with a view of her breasts. The seam of her bra was just visible in her hunched-over position. It felt like too long had passed before he realized he was looking down his boss’ blouse and his head jerked back up to look at her face, expecting disgust. But there was none. She was carefully mopping at his eyes to avoid poking him and pressed the tissue to his nose. “Blow.” Instinct took over and he blew into it, only feeling embarrassment at his own actions after she cleaned up his nose and tossed the tissue into the wastebasket. “Are you calm now?” She asked, positioning her hands on her knees and Jesse had to force himself not to peek back down at her cleavage. “Yes, Ma’am,” He nodded. “Good boy,” She purred. “Now come here.” Jesse found himself standing from his seat and being led around the desk to where Miss Tammy settled down in her own chair. He could see her heels tucked neatly under the desk and traced the path to her bare feet, up her shapely legs, to her her knees where her skirt was rucked almost too far up her thighs, and- Christ. At this angle he was able to see her breasts even better. The hem of her bra definitely peaking from the dip of her shirt now. Meeting her eyes, he blushed, seemingly caught. “You’ve been naughty this weekend,” She said with a sigh, one leg coming up to daintily cross over the other. “We have to figure out what to do about that.” Jesse frowned, worry creeping in. “I’m-” “Uh uh!” She tsked. “I’m talking, you listen. Understood?” “Yes, Ma’am.” Jesse nodded immediately. “Good boy,” The praise lifted his heart from where it seemed to have fallen right to the basement. “So,” She continued. “You were very naughty this weekend. You told me you were going to your brother’s birthday party, correct?” “Yes, Ma’am,” Jesse fought off the urge to elaborate. “And at this party you smoked weed,” Jesse’s eyes ducked to his feet guiltily. “And now I need to find a way to keep John from firing you.” “...Yes, Ma’am.” “Well, it’s a good thing you’re my favorite. Isn’t it, baby?” She chuckled. Hopefully, Jesse met her eyes, seeing a mischievous look peeking up from the rim of her glasses. A few seconds passed and he realized she was waiting for an answer. “Yes, Ma’am.” He found himself meeting that look with a small smile. “Now,” She rotated slightly back and forth in her seat. “I know how to save your job…but about what you can do for me as repayment.” Jesse blinked in surprise. Seconds ago, it felt as though his job hung by a thread. But now here he was with the reassurance he’d keep his job. Only with the added mystery of suddenly being indebted to Miss Tammy. Never did she ask for repayment for things. Whenever he tried to pass her money for the treats and things she’d give him, she always refused. But…he reasoned, she was saving his job. “I’ll do anything.” He swore. “Anything you want.” “Oh baby,” She laughed warmly. “You don’t want to tell me that.” “But I do,” He assured, crouching down, hell, nearly kneeling at her feet just to look up into her eyes. “You’ve done so much for me. You didn’t even have to tell me about the drug tests but you did. And- And,” He stuttered. “You’ve always treated me nicely. I’ll do anything to repay you for saving my job.” Her lips pursed in thought. “Anything?” “Yes! I’ll detail your car! Or pick up your dry cleaning! Hell, I’d scrub the floors of your house with my toothbrush if you asked me to,” He laughed at the image in his brain of him hunched fetal on what he imagined to be her kitchen floor. A flush overtook his face as he thought of her standing right in front of him. Towering and demanding as he worked hard to please her. “Take your pants off,” The words cut through his imagination. “What?” He asked, seeing her strict look once more on her face. “I said,” She spoke clearly but it might as well have been a yell in the quiet office. “Take. Your pants. Off.” Mouth suddenly dry, Jesse stood up. Was this really happening? It was a plot out of a bad porno, he was sure. He was dreaming! No way was his attractive boss demanding he take his pants off in response to her saving his job. “Well,” She quirked a brow and nodded to his belt. “Are you going to do it, or do I need to call John down here to start working on termination paperwork.” Jesse’s hands were on his belt the next second. His fingers shook as they fiddled with the loops and his cock already started to harden in his boxers. “M-Ma’am, Are we going to-” His question was halted as she suddenly shot forward and smacked his hands away from his belt. Her perfectly manicured fingers pulled at the belt until it dangled open. His pants slackened slightly on his hips. She didn’t stop there, unbuttoning his pants and sliding his fly down with ease. The pants pooled on the floor, his tented boxers left to hide his dick from his boss’ view. Her severe look didn’t change as she looked from his crotch to his face. Her legs uncrossed and her thighs parted. The skirt she wore rode higher on her thighs until he could almost see what color panties she wore. “Come here.” Jesse didn’t need to be told twice as he stepped into the space left between her thighs. His cock brushed against her skirt and would have left a smear of pre-cum had it not already been soaked up by his boxers. Jesse ducked his head to meet her lips, but found himself suddenly knocked off balance and turning. His fall was caught by the hard wooden desk and a firm hand came to press down on his spine to keep him from getting back up. “T-Tamera?” He asked in confusion only to feel a sudden sting radiate from his backside that startled a yelp out of him. His knees went weak but his weight was supported by the desk and hand holding him to it. “What did you just call me?” He heard Miss Tammy’s voice seethe in his ear. “Tamera?” Another sting brought out a hiss of pain. “Fuck!” Another SWAT. And he suddenly realized what was happening. He was being spanked! “Don’t you swear at me, boy!” Miss Tammy scolded. “You come into my office and beg me to save your naughty ass, you don’t get to swear at me.” “I’m sorry, Miss Tammy!” He gasped and yelped at another SWAT as it descended. The pain was fierce now. A sharp throb in his ass cheeks as she had been alternating which one she hit. “You’ve lost that privilege to, naughty little boy!” “Please!” He gasped as three spanks rained on his ass. How a hand as gentle and small as hers could create such force, he wasn’t sure. “I’m sorry!” “Tell Mommy how sorry you are,” Miss Tammy sneered. “Tell Mommy!” “I’m so sorry-” Three more spanks and Jesse felt his legs dance in place on the carpet. “Mommy!” The word was startled out of him as quickly as the blows stopped. A whimper tumbled from his lips as he anticipated another that didn’t come. “Say it again,” Miss Tammy’s gentle voice came once more. “Tell Mommy how sorry you are for being a naughty boy.” “I’m so sorry, Mommy,” Jesse’s lip quivered and he found himself dangerously close to tears once more. Air brushed against his red-hot ass and he rushed to continue before the blow came. “I’m sorry for being a naughty boy, Mommy!” “That’s better,” She sighed and the firm hand on his back loosened. He didn’t dare move though. “You like being my good boy, yeah?” “Yes, Mommy,” Jesse nodded, his hot face gaining relief from the cold surface of the desk. The hand on his back lifted and Jesse heard her sit back down. “Come here, baby.” Standing up and turning around, Jesse’s gaze dropped to Miss Tammy’s crotch. He had no idea when she’d taken her skirt off, but it lay on the floor near his pants. Her red lace panties were out on display for him to see. His eyes jumped from her pussy lips peaking from the thin fabric to her eyes staring at him intently. The red of her panties matched the red of her glasses, he realized. “Kneel right here for Mommy,” She pointed right between her legs and Jesse didn’t even register the burn of the carpet on his bare knees as he complied. This close, he could see where he slick was darkening the crotch of her panties. Could practically smell her arousal. His dick, having softened rapidly at the spanking, thickened up despite the residual throbs of his ass. “You took your punishment like a good little boy,” She commented and his eyes darted back up to see her smirking. Her thighs parted just a little more and her back bowed to push her hips closer to the edge of the chair. “Does baby like what he sees?” “Yes, Mommy,” Jesse nodded. Licking his lips. He could count on one hand the number of women he’d been with. And the things he did with them were mounting up to be laughably vanilla in comparison to this roleplay. He couldn’t say it wasn’t exciting even with how confusing it was. “Well,” She sighed and pushed her hips forward again. “Go on.” Needing no other invitation, Jesse found himself devouring the feast right in front of him. He pulled her panties to the side and with what he lacked in experience, he hoped he made up for in eagerness. Miss Tammy’s legs came to rest on his shoulders and her hand tangled in his hair. He didn’t know how long he ate her out, but he did so feverishly, chasing the slick from between her lips to the bud of her clit. Occasionally, he’d secure his lips in a suck around it, earning a sharp tug of his hair and an appreciative moan from Miss Tammy- Mommy. “Mommy’s gonna cum, baby,” She panted. If possible, Jesse redoubled his efforts. Digging his tongue deep into her folds til his chin was covered in her taste, he couldn’t help a mirrored moan with her as she pulled him close through her trembling orgasm. Jesse didn’t stop until the hand in his hair was pulling him away from her twitching cunt instead of closer. Her knees trembled on his shoulders. Rocking his own hips forward, Jesse felt his cock was begging for attention in his boxers. But when his hand reached down from where it rested against the outside of Mommy’s- Miss Tammy’s thigh to stroke himself off, her hand tightened in his hair once more. “Did I give you permission to touch yourself?” She scolded breathlessly. “N-No, Mommy,” Jesse whimpered, hand coming back to rest on her thigh. “That’s right,” She nodded and slowly slid her legs off his shoulder. She reached over and slid open her side desk drawer and pulled out a package of baby wipes. “Bring me my trashcan.” Slowly, Jesse stood up from his kneeled position and retrieved the wastebasket on the other side of the desk. Miss Tammy was using the baby wipes to wipe her pussy lips down and had since slipped her panties off. The panties remained in her hand when she tossed the wipes in the trash and she reached for his boxers. Thinking it was his turn to cum, Jesse helped her by shimmying them off, awkwardly pulling the fabric down past his shoes. He didn’t expect Miss Tammy to hold out her damp panties for him to step into, but when he looked into her eyes, she wasn’t bluffing. As he thought before, a seriously weird roleplay. But he couldn’t deny it was pretty hot. Before the panties were pulled up to his crotch, Jesse gasped as a cold wipe was pressed against his hard-on. “That’s it,” Miss Tammy smirked. “Shrink back down.” It took a few cold wipes before his dick was soft once more, although the thrum of arousal was still present. She pulled her panties up his thigh, his dick actually fitting in the small pocket in the front, although the fabric slid up the crack of his ass uncomfortably. “Put your pants back on.” She demanded. Jesse turned around, receiving a playful swat to his aching backside, and grabbed his pants from the floor. Miss Tammy helped him button and zip his pants and secure his belt once more. “Those will stay on for the rest of the day and you will come to my home instead of yours after work, understood?” “Yes, Ma’am,” Jesse spoke softly. “It’s Mommy whenever it’s just you and I,” She informed. “Understood?” “Yes, Mommy,” Jesse corrected and watched her slip her skirt back on and rebutton her blouse to hide her bra- wait…had she done that on purpose? “You’re free to return to work, baby,” She said in her usual professional tone. “Go on.” Jesse was stunned. That was it? Miss Tammy made a shooing motion with her hand and Jesse slowly shuffled to the door, the fabric of her panties digging into his skin teasingly. “See you tonight…Mommy,” He muttered and dipped out of the room. Taking a detour to the bathroom, not to take off the panties, but to fix his hair and wipe the cum from his lips. Just what did he get himself into?